14401-61-7

Usage

Uses

Used in Environmental Testing and Research:
2,4,5-Tribromophenol is used as a standard for environmental testing and research to determine the presence and concentration of urinary bromophenols (BrPs). These bromophenols serve as potential biomarkers for human exposure to polybrominated diphenyl ethers (PBDEs), which are a group of persistent organic pollutants known for their adverse effects on human health and the environment.
Used in Analytical Chemistry:
In the field of analytical chemistry, 2,4,5-tribromophenol is utilized as a reference compound for the development and validation of analytical methods. One such method involves the use of gas chromatography-tandem mass spectrometry (GC-MS/MS) to accurately measure and identify BrPs in various environmental and biological samples.
Used in Toxicological Studies:
2,4,5-Tribromophenol is also employed in toxicological studies to investigate the inhibitory potency of specific PBDE congeners, such as BDE-47 and BDE-99, on the cytochrome P450 2B6 (CYP2B6)-mediated metabolism of various compounds, including the pharmaceutical drug bupropion. This helps researchers understand the potential interactions between PBDEs and other chemicals in the human body, which can have implications for human health risk assessment.

InChI:InChI=1/C6H3Br3O/c7-3-1-5(9)6(10)2-4(3)8/h1-2,10H

Upstream product

• 591-20-8 3-Bromophenol 
• 608-71-9 Pentabromophenol 
• 615-86-1 2,4,5-tribromoaniline 
• 28165-52-8 2,5-dibromophenol 
• 14400-94-3 2,3,4,6-tetrabromophenol 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 98-95-3 nitrobenzene 
• 64-19-7 acetic acid 
• 615-56-5 3,4-dibromophenol 
• 108-95-2 phenol 
• 3147-55-5 3,5-dibromosalicylic acid 
• 855429-70-8 2,4,5-tribromophenyl acetate 
• 110-89-4 piperidine 

Downstream Products

• 95970-10-8 2,4,5-tribromo-anisole 
• 14400-94-3 2,3,4,6-tetrabromophenol 
• 60348-60-9 2,2',4,4',5-pentrabromodiphenyl ether 
• 68631-49-2 2,2',4,4',5,5'-hexabromobiphenyl ether 
• 725714-49-8 3,4,6-tribromo-2-nitro-anisole 
• 815578-59-7 3,4,6-tribromo-2-nitro-phenol 
• 25779-26-4 2,3,5-tribromo-1,4-benzoquinone 
• 207122-16-5 2,3,4,6-tetrabromophenyl 2,4,5-tribromophenyl ether 

Related news

Quantum chemical and direct dynamic study on homogeneous gas-phase formation of PBDD/Fs from 2,4,5-TRIBROMOPHENOL (cas 14401-61-7) and 3,4-dibromophenol08/15/2019

2,4,5-Tribromophenol (2,4,5-TBP) and 3,4-dibromophenol (3,4-DBP) have the minimum number of Br atoms needed to form 2,3,7,8-PBDD/Fs, which are the most toxic among all 210 PBDD/F isomers. A mechanistic understanding of the formation of PBDD/Fs is a prerequisite for minimizing their emissions. In...detailed

Relevant academic research and scientific papers

Polybrominated diphenyl ethers (BDEs); preparation of reference standards and fluorinated internal analytical standards

Four new difluorinated tetra- and pentabromo BDE internal standards for GC-MS/GC-ECD analysis, 2F-BDE 47, 2F-BDE 85, 2F-BDE 99 and 2F-BDE 119, have been prepared in 98-99.0% purity, mainly by coupling of the new tribromodifluorophenols (19-21) and symmetr

Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma

A growing number of studies have reported phenolic halogenated compounds (PHCs) that are retained in the blood of humans and wildlife. These PHCs may be industrial chemicals; metabolites thereof, as in the case with polychlorobiphenylols (OH-PCBs); or of natural origin. The present study was aimed to identify hitherto unknown PHCs in human plasma with chemical structures that are consistent to PHCs known to possess endocrine-disrupting activity. For this purpose, samples of blood plasma from 10 randomly selected male blood donors from Sweden were pooled and analyzed by GC/ECD and GC/MS. Brominated, bromochlorinated, and chlorinated methyl derivatives of phenols and OH-PCBs were synthesized to be used as authentic reference standards. More than 100 PHCs were indicated in the plasma, and among those a total of 9 monocyclic brominated or chlorinated phenol-, guaiacol-, and/or catechol-type compounds were identified as their methylated derivatives. The two major compounds were 2,4,6-tribromophenol and pentachlorophenol. Thirty-eight OH-PCB congeners were structurally identified on two GC columns of different polarity. The origin of the OH-PCB metabolites in the context of their parent PCB congeners are suggested. Other PHCs identified in the male plasma were Triclosan (5-chloro-2-[2,4-dichlorophenoxy] phenol), a common bactericide; 4-hydroxy-heptachlorostyrene, a metabolite of octachlorostyrene; and 3,5-dibromo-2-(2,4-dibromophenoxy)phenol, a natural compound and a potential metabolite of polybrominated diphenyl ethers.

Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah receptor mediated pathway

Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyre-sorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10-2-10-5 times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition sequence.

Process for producing polyhalogenated phenols

A process for producing polyhalogenated phenol by mixing a polyhalogenated aniline with an aqueous sulfuric acid solution to obtain a suspension of fine particles of polyhalogenated aniline sulfate having the particle size of 50 μ or less, diazotizing the polyhalogenated aniline sulfate to obtain polyhalogenate benzenediazonium sulfate, hydrolyzing the resulting benzenediazonium sulfate by heating it as such, recycling to the diazotization step the aqueous sulfuric acid solution from which the desired polyhalogenated phenol has been separated.